Synthesis and hybridization properties of an oligonucleotide analog containing a glucose-derived conformation-restricted ribose moiety and 2', 5' formacetal linkages

Tetrahedron Letters

Volumn 37, Issue 7, 1996, Pages 941-944

  Zou, Ruiming ^a   Matteucci, Mark D ^a  

^a GILEAD SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTISENSE OLIGONUCLEOTIDE; NUCLEOTIDE DERIVATIVE; OLIGONUCLEOTIDE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; RNA HYBRIDIZATION;

EID: 0030042618     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02396-8     Document Type: Article

References (21)

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6. c) Tarkov, M.; Bolli, M.; Leumann, C. Helv. Chim. Acta 1994, 77, 716.
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11. Modeling studies performed using Biograf software from Molecular Simulations Inc. The principle conformational restriction within this analog is the freezing of rotation about the C5' -O5' bond thereby fixing a gauche relationship between the O4' and O5'. The ribose ring pucker is likely locked in a 3' endo (A helix like) conformation by the 2' oxygen substituent.
12. Compound 2 had been prepared previously from 1, 2, 5, 6-diisopropylidene-D-glucose via a four-step synthesis (Ernie Prisbe, personal communication).
13. Quaedflieg, P.J.L.M.; Timmers, C.M.; van der Marel, G.A.; Kuyl-Yeheskiely, E.; van Boom, J.H. Synthesis 1993, 627.
14. 9
15. Zhang, L.; Matteucci, M.D. Tetrahedron Lett., submitted.
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17. 9
18. Froehler, B.C.; Ng, P.G.; Matteucci, M.D. Nucl. Acids Res. 1986, 14, 5399.
19. 2 and pH 7.2. These salt conditions were chosen to approximate the intracellular cationic environment. See: Alberts, B.; et al. Molecular Biology of the Cell; Garland: New York, 1989: p. 301.
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21. b) Milligan, J.F.; Matteucci, M.D.; Martin, J.C. J. Med. Chem. 1993, 36, 1923.